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Namingaromaticcompounds

THENAMESOFAROMATIC
COMPOUNDS
Thispagelooksatthenamesofsomesimplearomatic
compounds.Anaromaticcompoundisonewhichcontainsa
benzenering.Itassumesthatyouarereasonablyconfident
aboutnamingcompoundscontainingchainsofcarbonatoms
(aliphaticcompounds).
Note:Ifyouaren'tsureaboutnamingaliphaticcompounds
followthislinkbeforeyougoon.

Namingaromaticcompoundsisn'tquitesostraightforwardas
namingchaincompounds.Often,morethanonenameis
acceptableandit'snotuncommontofindtheoldnamesstillin
useaswell.

Background
Thebenzenering
Allaromaticcompoundsarebasedonbenzene,C6H6,which
hasaringofsixcarbonatomsandhasthesymbol:

Eachcornerofthehexagonhasacarbonatomwithahydrogen
attached.
Note:Ifyoudon'tunderstandthisstructure,itisexplainedin
fullintwopagesonthestructureofbenzeneelsewherein
thissite.Followingthislinkcouldwelltakeyousometime!

Thephenylgroup
Rememberthatyougetamethylgroup,CH3,byremovinga
hydrogenfrommethane,CH4.

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Yougetaphenylgroup,C6H5,byremovingahydrogenfroma
benzenering,C6H6.Likeamethyloranethylgroup,aphenyl
groupisalwaysattachedtosomethingelse.

Aromaticcompoundswithonlyonegroupattached
tothebenzenering
Caseswherethenameisbasedonbenzene
chlorobenzene
Thisisasimpleexampleofahalogenattachedtothebenzene
ring.Thenameisselfobvious.

ThesimplifiedformulaforthisisC6H5Cl.Youcouldtherefore
(althoughyouneverdo!)callitphenylchloride.Wheneveryou
drawabenzeneringwithoneotherthingattachedtoit,youare
infactdrawingaphenylgroup.Inordertoattachsomething
else,youhavetoremoveoneoftheexistinghydrogenatoms,
andsoautomaticallymakeaphenylgroup.
nitrobenzene
Thenitrogroup,NO2,isattachedtoabenzenering.

ThesimplifiedformulaforthisisC6H5NO2.
methylbenzene
Anotherobviousnamethebenzeneringhasamethylgroup
attached.Otheralkylsidechainswouldbenamedsimilarlyfor
example,ethylbenzene.Theoldnameformethylbenzeneis
toluene,andyoumaystillmeetthat.

ThesimplifiedformulaforthisisC6H5CH3.
(chloromethyl)benzene
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Avariantonthiswhichyoumayneedtoknowaboutiswhere
oneofthehydrogensontheCH3groupisreplacedbyachlorine
atom.Noticethebracketsaroundthe(chloromethyl)inthe
name.Thisissothatyouaresurethatthechlorineispartofthe
methylgroupandnotsomewhereelseonthering.

Ifmorethanoneofthehydrogenshadbeenreplacedby
chlorine,thenameswouldbe(dichloromethyl)benzeneor
(trichloromethyl)benzene.Again,noticetheimportanceofthe
bracketsinshowingthatthechlorinesarepartofthesidegroup
andnotdirectlyattachedtothering.
benzoicacid(benzenecarboxylicacid)
Benzoicacidistheoldername,butisstillincommonuseit'sa
loteasiertosayandwritethanthemodernalternative!Whatever
youcallit,ithasacarboxylicacidgroup,COOH,attachedto
thebenzenering.

Caseswherethenameisbasedonphenyl
Rememberthatthephenylgroupisabenzeneringminusa
hydrogenatomC6H5.Ifyoudrawabenzeneringwithone
groupattached,youhavedrawnaphenylgroup.
phenylamine
PhenylamineisaprimaryamineandcontainstheNH2group
attachedtoabenzenering.

Theoldnameforphenylamineisaniline,andyoucouldalso
reasonablycallitaminobenzene.Phenylamineiswhatitismost
commonlyforUKbasedexampurposes.
Note:Inallcaseswherethereissomepossibilityof
alternativenames,youneedtoknowwhatyourexaminers
arelikelytocallaparticularcompound.Refertoyour
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syllabusandrecentexampapers.IfyouareworkingtoaUK
basedsyllabusfor168yearolds,andhaven'tgotthese,
followthislinktofindouthowtogetholdofthem.

phenylethene
Thisisanethenemoleculewithaphenylgroupattached.
Etheneisatwocarbonchainwithacarboncarbondoublebond.
Phenyletheneistherefore:

Theoldnameforphenyletheneisstyrenethemonomerfrom
whichpolystyreneismade.
phenylethanone
Thisisaslightlyawkwardnametakeittopieces.Itconsistsof
atwocarbonchainwithnocarboncarbondoublebond.The
oneendingshowsthatitisaketone,andsohasaC=Ogroup
somewhereinthemiddle.Attachedtothecarbonchainisa
phenylgroup.Puttingthattogethergives:

phenylethanoate
Thisisanesterbasedonethanoicacid.Thehydrogenatomin
theCOOHgrouphasbeenreplacedbyaphenylgroup.

Note:Ifyouaren'thappyaboutnamingesters,followthis
linkbeforeyougoon.

phenol
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PhenolhasanOHgroupattachedtoabenzeneringandso
hasaformulaC6H5OH.

Aromaticcompoundswithmorethanonegroup
attachedtothebenzenering
Numberingthering
Anygroupalreadyattachedtotheringisgiventhenumber1
position.Whereyoudrawitonthering(atthetoporinanyother
position)doesn'tmatterthat'sjustaquestionofrotatingthe
moleculeabit.It'smucheasier,though,togetinthehabitof
drawingyourmaingroupatthetop.
Theotherringpositionsarethennumberedfrom2to6.Youcan
numberthemeitherclockwiseoranticlockwise.Aswithchain
compounds,younumbertheringsothatthenameyouendup
withhasthesmallestpossiblenumbersinit.Exampleswillmake
thisclear.
Somesimpleexamples
Substitutingchlorineatomsonthering
Lookatthesecompounds:

Allofthesearebasedonmethylbenzeneandsothemethyl
groupisgiventhenumber1positiononthering.
Whyisit2chloromethylbenzeneratherthan6
chloromethylbenzene?Theringisnumberedclockwiseinthis
casebecausethatproducesa2inthenameratherthana6.2
issmallerthan6.
Warning!Youwillfindallsortsofvariationsonthis
dependingontheageofthebookyoulookitupin,andwhere
itwaspublished.WhatIhavedescribedaboveisn'tinstrict
accordancewiththemostmoderninterpretationoftheIUPAC
recommendationsfornamingorganiccompounds.
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Thenamesshouldactuallybe1chloro2methylbenzene,1
chloro3methylbenzene,andsoon.Thesubstitutedgroups
arenamedinalphabeticalorder,andthe"1"positionis
assignedtothefirstoftheseratherthantothemorelogical
methylgroup.
Thisproducessomesillyinconsistencies.Forexample,if
youhadtheexactlyequivalentcompoundscontainingnitro
groupsinplaceofthechlorines,thenameswouldchange
completely,to1methyl2nitrobenzene,1methyl3
nitrobenzene,etc.Inthiscase,thenormalpracticeofnaming
thehydrocarbonfirst,andthenattachingotherthingstoit
hasbeencompletelywrecked.
Doyouneedtoworryaboutthis?NO!Itisextremelyunlikely
thatyouwouldeverbeaskedtonametheseinanexam,and
itisalwayseasytowriteastructurefromoneofthese
nameshoweverillogicalitmaybe!Thereisasimplerulefor
exampurposes.Unlessyouarespecificallyaskedforthe
nameofanythingremotelycomplicated,don'tgiveit.Aslong
asyouhavegotthestructureright,that'sallthatmatters.

2hydroxybenzoicacid
Thismightalsobecalled2hydroxybenzenecarboxylicacid.
ThereisaCOOHgroupattachedtotheringand,becausethe
nameisbasedonbenzoicacid,thatgroupisassignedthe
number1position.Nextdoortoitinthe2positionisahydroxy
group,OH.

benzene1,4dicarboxylicacid
Thedishowsthattherearetwocarboxylicacidgroups,COOH,
oneoftheminthe1positionandtheotheroppositeitinthe4
position.

2,4,6trichlorophenol
ThisisbasedonphenolwithanOHgroupattachedinthe
number1positiononthering.Thereare3chlorineatoms
substitutedontotheringinthe2,4and6positions.

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methyl3nitrobenzoate
Thisisanameyoumightcomeacrossasapartofapractical
exerciseinnitratingbenzenerings.It'sincludedpartlyforthat
reason,andpartlybecauseitisarelativelycomplicatednameto
finishwith!
Thestructureofthenameshowsthatitisanester.Youcantell
thatfromtheoateending,andthemethylgroupfloating
separatelyfromtherestofthenameatthebeginning.
Theesterisbasedontheacid,3nitrobenzoicacidsostartwith
that.
TherewillbeabenzeneringwithaCOOHgroupinthenumber
1positionandanitrogroup,NO2,inthe3position.TheCOOH
groupismodifiedtomakeanesterbyreplacingthehydrogenof
theCOOHgroupbyamethylgroup.
Methyl3nitrobenzoateistherefore:

Questionstotestyourunderstanding
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onyourbrowsertocomebackhereafterwards.
questionsonnamingaromaticmolecules
answers

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